HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$139+ Cheap flights from Calgary (YYC) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/2. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Calgary to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Calgary to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 12, 2025.

Round-trip from

$240
(Delta)

One-way from

$139
(Delta)

Popular in

December

Cheapest in

April

Average price

$244
From Calgary to Chicago Midway
Search Deals
One-way flight from Calgary to Chicago Midway
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

Find flight deals from Calgary to Midway

Cheapest flights from Calgary to Midway
Explore the most affordable flight options available from Calgary to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/176:45 amYYC - MDW
1 stop9h 55mDelta
Tue 6/241:47 pmMDW - YYC
1 stop8h 10mDelta
Deal found 6/11$240
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2512:30 amYYC - MDW
1 stop21h 05mMultiple Airlines
Sat 8/26:20 amMDW - YYC
2 stops19h 24mMultiple Airlines
Deal found 6/11$348
This Mytrip deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/217:00 amYYC - MDW
2 stops32h 24mPorter Airlines
Tue 8/55:20 pmMDW - YYC
2 stops29h 00mPorter Airlines
Deal found 6/11$460
This Jettzy deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2512:30 amYYC - MDW
1 stop20h 12mWestJet
Sat 8/212:43 pmMDW - YYC
1 stop10h 32mWestJet
Deal found 6/11$645

Cheapflights Fare Finder

Customize your flight search to find flights from Calgary to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
Use the filters below to find and compare flights from Calgary to Chicago Midway Airport that are best for you.

Fly from

Calgary

Fly to

Midway

Route

Depart

Return

Price

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/9

6:40 am-5:37 pm

1 stop9h 57m

Chicago Midway

Wed 9/17

1:00 pm-8:54 pm

2 stops8h 54m

$240

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 7/25

12:30 am-10:35 pm

1 stop21h 05m

Chicago Midway

Sat 8/2

6:20 am-12:44 am

2 stops19h 24m

$348

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 7/21

7:00 am-4:24 pm

2 stops32h 24m

Chicago Midway

Tue 8/5

5:20 pm-9:20 pm

2 stops29h 00m

$460

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 7/25

12:30 am-9:42 pm

1 stop20h 12m

Chicago Midway

Sat 8/2

12:43 pm-10:15 pm

1 stop10h 32m

$645

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 7/2

6:45 am-5:40 pm

1 stop9h 55m

$139

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 7/8

12:30 am-10:40 am

1 stop9h 10m

$169

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 7/28

11:55 pm-4:24 pm

2 stops15h 29m

$222

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 8/18

12:30 am-9:16 am

1 stop7h 46m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Best time to book a flight from Calgary to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Calgary with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Calgary to Chicago Midway Airport

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated June 12, 2025.
To help decide which airline to fly from Calgary to Chicago, see what other customers have to say about Porter Airlines, Delta and WestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
288 reviews

Entertainment

7.0

Crew

8.7

Overall

8.0

Comfort

8.1

Boarding

8.2

Food

7.6

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews

Entertainment

7.0

Crew

8.7

Overall

8.0

Comfort

8.1

Boarding

8.2

Food

7.6

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,950 reviews
Porter Airlines
8.0
Very good
288 reviews

Entertainment

7.0

Crew

8.7

Overall

8.0

Comfort

8.1

Boarding

8.2

Food

7.6

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,868 reviews
Porter Airlines
8.0
Very good
288 reviews

Entertainment

7.0

Crew

8.7

Overall

8.0

Comfort

8.1

Boarding

8.2

Food

7.6

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Related info for your journey

Find useful and relevant information for your journey from Calgary to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Calgary to Chicago Midway?

    For a flight from Calgary to Chicago Midway, you will be flying from Calgary. Calgary (YYC) is just 5.8 mi from the center of the city. Calgary is the only Calgary airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from Calgary on a regular basis.

  • What are the cheapest airlines flying from Calgary to Chicago Midway Airport round-trip?

    Our cheapest airline available from Calgary to Chicago Midway Airport is Delta. Our recent data shows that you can find tickets from as low as $240 on this airline. Additional options worth looking into are Porter Airlines and WestJet, starting at $460 and $645 round-trip.

  • What are the cheapest airlines to fly from Calgary to Chicago Midway Airport one-way?

    $139 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Porter Airlines and WestJet, with prices starting from $222 and $361, respectively.

  • Can I find deals for flights from Calgary to Midway that include hotel bookings?

    Yes. In addition to deals on Calgary to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Calgary to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Calgary to Midway.

  • Can I find deals for business class flights from Calgary to Midway?

    Yes. Cheapflights offers flight deals from Calgary to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Calgary to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Calgary to Chicago Midway Airport (average of $160). Flying from Calgary to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Calgary?

Book flights to Calgary if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Calgary to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Calgary to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Edmonton to Midway flights
Grande Prairie to O'Hare Intl flights
Medicine Hat to O'Hare Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.